JP6458270B2 - 置換されたヒドロキサム酸化合物 - Google Patents

置換されたヒドロキサム酸化合物 Download PDF

Info

Publication number
JP6458270B2
JP6458270B2 JP2016534884A JP2016534884A JP6458270B2 JP 6458270 B2 JP6458270 B2 JP 6458270B2 JP 2016534884 A JP2016534884 A JP 2016534884A JP 2016534884 A JP2016534884 A JP 2016534884A JP 6458270 B2 JP6458270 B2 JP 6458270B2
Authority
JP
Japan
Prior art keywords
alkyl
alkoxy
compound
heteroaryl
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
JP2016534884A
Other languages
English (en)
Japanese (ja)
Other versions
JP2016535758A (ja
JP2016535758A5 (OSRAM
Inventor
ジョウ ペイ
ジョウ ペイ
ジェイ.トゥーン エリック
ジェイ.トゥーン エリック
エー.ニコラス ロバート
エー.ニコラス ロバート
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of North Carolina at Chapel Hill
Duke University
Original Assignee
University of North Carolina at Chapel Hill
Duke University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of North Carolina at Chapel Hill, Duke University filed Critical University of North Carolina at Chapel Hill
Publication of JP2016535758A publication Critical patent/JP2016535758A/ja
Publication of JP2016535758A5 publication Critical patent/JP2016535758A5/ja
Application granted granted Critical
Publication of JP6458270B2 publication Critical patent/JP6458270B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/63One oxygen atom
    • C07D213/64One oxygen atom attached in position 2 or 6
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Pyridine Compounds (AREA)
JP2016534884A 2013-08-16 2014-08-18 置換されたヒドロキサム酸化合物 Expired - Fee Related JP6458270B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361866823P 2013-08-16 2013-08-16
US61/866,823 2013-08-16
US201361867933P 2013-08-20 2013-08-20
US61/867,933 2013-08-20
PCT/US2014/051459 WO2015024010A2 (en) 2013-08-16 2014-08-18 Substituted hydroxamic acid compounds

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2018224004A Division JP2019077688A (ja) 2013-08-16 2018-11-29 置換されたヒドロキサム酸化合物

Publications (3)

Publication Number Publication Date
JP2016535758A JP2016535758A (ja) 2016-11-17
JP2016535758A5 JP2016535758A5 (OSRAM) 2017-09-28
JP6458270B2 true JP6458270B2 (ja) 2019-01-30

Family

ID=52468825

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2016534884A Expired - Fee Related JP6458270B2 (ja) 2013-08-16 2014-08-18 置換されたヒドロキサム酸化合物
JP2018224004A Pending JP2019077688A (ja) 2013-08-16 2018-11-29 置換されたヒドロキサム酸化合物

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2018224004A Pending JP2019077688A (ja) 2013-08-16 2018-11-29 置換されたヒドロキサム酸化合物

Country Status (6)

Country Link
US (1) US10647664B2 (OSRAM)
EP (1) EP3041354A4 (OSRAM)
JP (2) JP6458270B2 (OSRAM)
AU (1) AU2014306451B2 (OSRAM)
CA (1) CA2921427A1 (OSRAM)
WO (1) WO2015024010A2 (OSRAM)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019077688A (ja) * 2013-08-16 2019-05-23 デューク ユニバーシティ 置換されたヒドロキサム酸化合物

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2015261540A1 (en) 2014-05-16 2017-01-12 Idorsia Pharmaceuticals Ltd Antibacterial quinazoline-4(3h)-one derivatives
US10414735B2 (en) 2015-11-09 2019-09-17 Forge Therapeutics, Inc. Substituted hydroxypyrimidinones for treating bacterial infections
WO2017083434A1 (en) 2015-11-09 2017-05-18 Forge Therapeutics, Inc. Pyrone based compounds for treating bacterial infections
ES2961564T3 (es) 2016-04-25 2024-03-12 Univ Duke Derivados de benzoilglicina y métodos de preparación y uso de los mismos
JP7471820B2 (ja) * 2016-12-23 2024-04-22 インターベット インターナショナル ベー. フェー. マンヘミア・ヘモリチカ感染症又はヒストフィルス・ソムニ感染症を治療するのに有用な化合物
WO2018208985A2 (en) 2017-05-10 2018-11-15 Forge Therapeutics, Inc. Antibacterial compounds
SG11202007665RA (en) * 2018-02-10 2020-09-29 Kbp Biosciences Co Ltd Compound acting as antibiotics
CA3113226A1 (en) * 2018-09-20 2020-03-26 Forge Therapeutics, Inc. Antibacterial compounds
WO2021195260A1 (en) 2020-03-25 2021-09-30 Forge Therapeutics, Inc. Lpxc inhibitor and methods of making
KR20230066379A (ko) 2020-09-09 2023-05-15 크리네틱스 파마슈티칼스, 인크. 소마토스타틴 조절제 제형
AU2022357226A1 (en) 2021-09-28 2024-05-02 Blacksmith Medicines, Inc. Lpxc inhibitors and uses thereof
WO2024077160A2 (en) * 2022-10-05 2024-04-11 Duke University Compositions comprising prodrugs of hydroxyamate-based compounds and methods of making and using same

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU3351293A (en) 1992-01-21 1993-08-03 Glaxo Group Limited Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation
TW448172B (en) 1996-03-08 2001-08-01 Pharmacia & Upjohn Co Llc Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation
US5925659A (en) 1996-05-07 1999-07-20 Merck & Co., Inc. Antibacterial agents
GB9725782D0 (en) 1997-12-05 1998-02-04 Pfizer Ltd Therapeutic agents
JP2000344752A (ja) * 1999-04-01 2000-12-12 Sumitomo Pharmaceut Co Ltd 点眼剤
US6511993B1 (en) 1999-06-03 2003-01-28 Kevin Neil Dack Metalloprotease inhibitors
EA012260B1 (ru) * 2002-01-29 2009-08-28 Лаборатуар Сероно Са ЗАМЕЩЁННЫЕ ПРОИЗВОДНЫЕ МЕТИЛЕНАМИДА В КАЧЕСТВЕ МОДУЛЯТОРОВ ПРОТЕИНТИРОЗИНФОСФАТАЗ (PTPs)
WO2003091247A2 (en) 2002-04-25 2003-11-06 Pharmacia Corporation Piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors
AU2003267991B2 (en) 2002-07-11 2009-10-08 Vicuron Pharmaceuticals, Inc. N-hydroxyamide derivatives possessing antibacterial activity
KR101076018B1 (ko) 2003-01-08 2011-10-21 유니버시티 오브 워싱톤 항균제
US20050154022A1 (en) 2004-01-14 2005-07-14 H. Lundbeck A/S 4-aryl piperidines
US7638513B2 (en) 2004-06-02 2009-12-29 Schering Corporation Compounds for the treatment of inflammatory disorders
AT502219B1 (de) 2005-08-04 2007-04-15 Sanochemia Pharmazeutika Ag Verfahren zur reindarstellung von 5-substituierten tetrazolen
EP1957449A1 (en) 2005-12-01 2008-08-20 Schering Corporation Compounds for the treatment of inflammatory disorders and microbial diseases
CN101528711A (zh) 2006-08-31 2009-09-09 先灵公司 可用作抗细菌剂的乙内酰脲衍生物
WO2008105515A1 (ja) 2007-02-28 2008-09-04 Taisho Pharmaceutical Co., Ltd. 新規なヒドロキサム酸誘導体
CA2691987C (en) 2007-06-12 2016-08-16 Achaogen, Inc. Antibacterial agents
US20110212078A1 (en) 2008-06-25 2011-09-01 Reddy Panduranga Adulla P Synthesis and use of heterocyclic antibacterial agents
WO2010017060A1 (en) 2008-08-04 2010-02-11 Schering Corporation Urea derivatives as antibacterial agents
WO2010024356A1 (ja) 2008-08-27 2010-03-04 大正製薬株式会社 ナフチリジン-n-オキシドを有する新規ヒドロキサム酸誘導体
US8372885B2 (en) 2008-09-17 2013-02-12 Novartis Ag Organic compounds and their uses
WO2010100475A1 (en) 2009-03-02 2010-09-10 Astrazeneca Ab Hydroxamic acid derivatives as gram-negative antibacterial agents
WO2011005355A1 (en) 2009-05-07 2011-01-13 Achaogen, Inc. Combinations comprising a lpxc inhibitor and an antibiotic for use in the treatment of infections caused by gram-negative bacteria
JP5671545B2 (ja) * 2009-10-13 2015-02-18 ファイザー・インク 抗菌薬として有用なc結合ヒドロキサム酸誘導体
US8389536B2 (en) 2009-10-27 2013-03-05 Hoffmann-La Roche Inc. Positive allosteric modulators (PAM)
CA2782453C (en) 2009-12-16 2015-11-24 Matthew Frank Brown N-linked hydroxamic acid derivatives useful as antibacterial agents
CA2796750C (en) * 2010-04-20 2017-09-19 Taisho Pharmaceutical Co., Ltd. Novel hydroxamic acid derivative
US9738604B2 (en) * 2010-09-03 2017-08-22 Duke University Ethynylbenzene derivatives
US8772300B2 (en) * 2011-04-19 2014-07-08 Hoffmann-La Roche Inc. Phenyl or pyridinyl-ethynyl derivatives
WO2013049255A1 (en) * 2011-09-26 2013-04-04 Vanderbilt University Substitued 5-(prop-1-yn-1-yl)picolinamide analogs as allosteric modulators of mglur5 receptors
JP6006609B2 (ja) * 2011-10-19 2016-10-12 大正製薬株式会社 新規なヒドロキサム酸誘導体を含有する医薬
EP2847168A1 (en) * 2012-05-10 2015-03-18 Achaogen, Inc. Antibacterial agents
CA2905248A1 (en) * 2013-03-15 2014-09-18 Muneo Shoji Novel hydroxamic acid derivative or salt thereof
JP6458270B2 (ja) * 2013-08-16 2019-01-30 デューク ユニバーシティ 置換されたヒドロキサム酸化合物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019077688A (ja) * 2013-08-16 2019-05-23 デューク ユニバーシティ 置換されたヒドロキサム酸化合物

Also Published As

Publication number Publication date
CA2921427A1 (en) 2015-02-19
US20160221934A1 (en) 2016-08-04
JP2019077688A (ja) 2019-05-23
WO2015024010A2 (en) 2015-02-19
US10647664B2 (en) 2020-05-12
EP3041354A4 (en) 2017-06-14
WO2015024010A3 (en) 2015-04-16
AU2014306451B2 (en) 2019-01-17
JP2016535758A (ja) 2016-11-17
AU2014306451A1 (en) 2016-03-03
EP3041354A2 (en) 2016-07-13

Similar Documents

Publication Publication Date Title
JP6458270B2 (ja) 置換されたヒドロキサム酸化合物
RU2712275C9 (ru) Замещенные полициклические производные пиридона и их пролекарства
US10597361B2 (en) Ethynylbenzene derivatives
RU2745071C2 (ru) Лекарственный препарат для лечения гриппа, характеризующийся тем, что в нем объединены ингибитор кэп-зависимой эндонуклеазы и лекарственное средство против гриппа
WO2018030463A9 (ja) 置換された多環性ピリドン誘導体およびそのプロドラッグを含有する医薬組成物
US9908851B2 (en) 2-piperidinyl substituted N,3-dihydroxybutanamides
US20240425447A1 (en) Benzoylglycine derivatives and methods of making and using same
JP2016505597A (ja) Prmt5阻害剤およびその使用
RS64012B1 (sr) Derivati supstituisanog policikličnog piridona i njihov prolek
US10189786B2 (en) Antibacterial compounds
WO2007149782A2 (en) Selective inhibitors for transferases
WO2024071371A1 (ja) 複素環式化合物

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20170818

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20170818

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20180426

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20180508

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20180807

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20181030

A711 Notification of change in applicant

Free format text: JAPANESE INTERMEDIATE CODE: A711

Effective date: 20181127

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20181129

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A821

Effective date: 20181127

R150 Certificate of patent or registration of utility model

Ref document number: 6458270

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

LAPS Cancellation because of no payment of annual fees